Method for the preparation of (3E,7E)-homofarnesic acid or (3E,7E)-homofarnesic acid ester

    公开(公告)号:US11136611B2

    公开(公告)日:2021-10-05

    申请号:US16487978

    申请日:2018-02-23

    Applicant: BASF SE

    Abstract: The invention provides an improved method of isolating the 3-(E)-isomer of an unsaturated carboxylic acid from a mixture of corresponding (E/Z)isomers. More particularly, the present invention relates to an improved method for the biocatalytic preparation of (3E,7E)-homofarnesylic acid; as well as a novel biocatalytic method for the improved preparation of homofarnesol, in particular of (3E,7E)-homofarnesol and homofarnesol preparations having an increased content of (3E,7E)-homofarnesol. The present invention also relates to methods of preparing(−)-ambroxby applying (3E,7E)-homofarnesylic acid or (3E,7E)-homofarnesol as obtained according to the invention as starting material.

    Method for synthesizing optically active carbonyl compounds

    公开(公告)号:US10301244B2

    公开(公告)日:2019-05-28

    申请号:US15964400

    申请日:2018-04-27

    Applicant: BASF SE

    Abstract: The present invention relates to a process for the preparation of an optically active carbonyl compound by asymmetric hydrogenation of a prochiral α,β-unsaturated carbonyl compound with hydrogen in the presence of at least one optically active transition metal catalyst that is soluble in the reaction mixture and which has rhodium as catalytically active transition metal and a chiral, bidentate bisphosphine ligand, wherein the reaction mixture during the hydrogenation of the prochiral α,β-unsaturated carbonyl compound additionally comprises at least one compound of the general formula (I): in which R1, R2: are identical or different and are C6- to C10-aryl which is unsubstituted or carries one or more, e.g. 1, 2, 3, 4 or 5, substituents which are selected from C1- to C6-alkyl, C3- to C6-cycloalkyl, C6- to C10-aryl, C1- to C6-alkoxy and amino; Z is a group CHR3R4 or aryl which is unsubstituted or carries one or more, e.g. 1, 2, 3, 4 or 5, substituents which are selected from C1- to C6-alkyl, C3- to C6-cycloalkyl, C6- to C10-aryl, C1- to C6-alkoxy and amino, wherein R3 and R4 are as defined in the claims and the description.

    Method for the isomerization of a 3-(Z)-unsaturated carboxylic acid to the 3-(E)-isomer

    公开(公告)号:US12172956B2

    公开(公告)日:2024-12-24

    申请号:US16969680

    申请日:2019-02-13

    Applicant: BASF SE

    Abstract: The present invention relates to a method for isomerizing a 3-(Z)-unsaturated carboxylic acid of the formula 1-Z or a salt thereof, wherein R2 is C1-C24-alkyl, C2-C24-alkenyl having 1, 2, 3 or more than 3 C—C double bonds, unsubstituted or substituted C5-C12-cycloalkyl, or unsubstituted or substituted aryl; R1 is hydrogen or has one of the definitions specified for R2; with the proviso that R2 has a higher priority than R1 in accordance with IUPAC; to give a 3-(E)-unsaturated carboxylic acid of the formula I-E or a salt thereof, wherein the isomerization of the compound of the formula 1-Z is effected in the presence of an anhydride of an organic acid and a base or in the presence of a ketene of formula CR11R12C(0), wherein R11 and R12 are as defined in the claims and in the specification and a base. In particular, the present invention relates to a method for preparing compositions with increased content of (3E,7E)-homofarnesylic acid starting from compositions comprising (3Z,7E)- and (3E,7E)-homofarnesylic acid.

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